Imitating anything - like Outlook - usually really ignites the spam filters. Anything that looks suspicious will stir them.
My experience is, that the more the mail looks like what it really is: sent from an "honest" automated system - the better.
I have made dozens of these systems before, including e-mail newsletters, confirmation, password reminders etc. but never had this problem before.
For some reason this particular setup trips the wire.
Martin